Careers

Build what comes next.

Join a team of high-agency people, and help the organizations of tomorrow become the organizations of later today.

Life at Core Systems Strategies

We hire for culture fit, culture add, and culture alignment.

Our people bring curiosity, conviction, and a willingness to revisit both in a follow-up meeting. We believe great work happens at the intersection of ambition and process, ideally in a room with a whiteboard.

01

Own the outcome

And the input, the throughput, and the follow-up on the throughput.

02

Disagree and commit

We encourage healthy debate, provided it concludes in commitment.

03

Bias for momentum

Forward is our preferred direction. Sideways is acceptable if framed as a pivot.

Open Roles

Find where you fit.

Head of AI Transformation

StrategyAI-native (remote)Full-time

Lead our transformation into an AI-first firm, and our clients’ transformations after that. You will define what AI means for Core Systems Strategies, then communicate it with confidence.

What you’ll do

  • Add “AI-powered” to our existing offerings.
  • Form an AI Council, then an AI Council working group.
  • Identify use cases, and use cases for the use cases.

What you’ll bring

  • No AI experience required.
  • Experience saying “AI” in meetings strongly preferred.
  • Comfort describing every pilot as “promising.”

Chief Alignment Officer

Executive LeadershipHybrid (mostly aligned)Full-time

The Chief Alignment Officer owns the end-to-end alignment roadmap, ensuring that every initiative is aligned with every other initiative, including the alignment roadmap itself.

What you’ll do

  • Define, socialize, and re-socialize the organization’s alignment priorities.
  • Chair the Alignment Council and its Alignment Sub-Council.
  • Report to the CEO, in alignment with the CEO.

What you’ll bring

  • 15+ years of alignment experience, at least three of them concurrent.
  • A demonstrated ability to nod meaningfully.

VP of Forward Momentum

StrategyRemote, but movingFull-time

The VP of Forward Momentum is responsible for maintaining organizational momentum in a forward direction. Momentum in any other direction will be escalated.

What you’ll do

  • Identify momentum. Sustain it. Report on it in a format that also has momentum.
  • Partner with Operations to ensure stillness is never mistaken for stability.

What you’ll bring

  • A track record of moving things forward, or of being near things as they moved forward.
  • Comfort with ambiguity, and with confidently resolving it.

Senior Synergy Architect

AdvisoryOn-siteFull-time

Our Synergy Architects design the structures within which synergies can be realized, or at least identified in a slide.

What you’ll do

  • Map interdependencies across functions, then map the interdependencies between the maps.
  • Translate client complexity into a two-by-two matrix.

What you’ll bring

  • Experience with both syn and ergy. Candidates with both together preferred.
  • Fluency in at least one framework, and a willingness to name another after yourself.

Director of Circling Back

CommunicationsHybridFull-time

The Director of Circling Back ensures that no conversation is ever truly concluded. You will own follow-ups, follow-ups on follow-ups, and the quarterly review of outstanding follow-ups.

What you’ll do

  • Take things offline, then bring them back online at the appropriate time.
  • Maintain the organization’s master list of things to touch base on.

What you’ll bring

  • Exceptional persistence. Gentle, recurring persistence.
  • Inbox Zero at least once, as an adult.

Associate, Strategic Pauses

OperationsOn-sitePart-time

Identify moments when the organization would benefit from stepping back to reflect, and schedule them for after the deadline.

What you’ll bring

  • Patience. A calendar. Ideally both.
Benefits

We invest in our people. Conceptually.

Unlimited PTO

Expected usage: aligned with business needs, which are unlimited.

Flexible hours

Work whichever hours you like, provided they are all of them.

Equity in our vision

Every team member receives a meaningful stake in where we are going.

Professional development

An annual Strategic Maturity assessment, with certificate.

A seat at the table

Table provided. Seating subject to alignment.

Wellness

Monthly mindfulness sessions on being present for the future.

Our Process

From conversation to offer, conceptually.

  1. Initial vibe checkA short conversation to confirm we are already in agreement.
  2. Values interviewWe discuss our values, then yours, then ours again.
  3. Case exerciseYou will be given a complex challenge and asked to operationalize it.
  4. Final roundA conversation with the final round.
How to Apply

All positions are currently filled by alignment.

We are not accepting applications at this time, as every open role has been absorbed into the roles around it. We encourage you to follow us on LinkedIn in the meantime.

In plain terms: Core Systems Strategies is a satirical publication, and these roles are not real. Please don’t send applications, résumés, or personal information. See our editorial note.